U.S. patent application number 15/367587 was filed with the patent office on 2017-06-08 for herbicidal compositions containing 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxyl- ic acid or derivative thereof, florasulam or derivative thereof, and pyroxsulam or derivative thereof.
This patent application is currently assigned to Dow AgroSciences LLC. The applicant listed for this patent is Dow AgroSciences LLC. Invention is credited to Roger E. Gast, Richard K. Mann.
Application Number | 20170156324 15/367587 |
Document ID | / |
Family ID | 58799406 |
Filed Date | 2017-06-08 |
United States Patent
Application |
20170156324 |
Kind Code |
A1 |
Gast; Roger E. ; et
al. |
June 8, 2017 |
HERBICIDAL COMPOSITIONS CONTAINING
4-AMINO-3-CHLORO-6-(4-CHLORO-2-FLUORO-3-METHOXYPHENYL)PYRIDINE-2-CARBOXYL-
IC ACID OR DERIVATIVE THEREOF, FLORASULAM OR DERIVATIVE THEREOF,
AND PYROXSULAM OR DERIVATIVE THEREOF
Abstract
Provided herein are herbicidal compositions and methods using a
mixture comprising (a) the compound of formula (I) ##STR00001## or
an agriculturally acceptable salt of ester thereof, (b) florasulam
or an agriculturally acceptable salt thereof, and (c) pyroxsulam or
an agriculturally acceptable salt thereof. The compositions provide
synergistic weed control of undesirable vegetation in areas
including, but not limited to, annual crop, cereal crop,
fallow-bed, non-crop, IVM, range and pasture, tree and vine crop,
perennial crop, fruiting crop, and plantation crop areas.
Inventors: |
Gast; Roger E.;
(Indianapolis, IN) ; Mann; Richard K.;
(Indianapolis, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Dow AgroSciences LLC |
Indianapolis |
IN |
US |
|
|
Assignee: |
Dow AgroSciences LLC
Indianapolis
IN
|
Family ID: |
58799406 |
Appl. No.: |
15/367587 |
Filed: |
December 2, 2016 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
62264519 |
Dec 8, 2015 |
|
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|
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 43/40 20130101;
A01N 43/42 20130101; A01N 43/90 20130101; A01N 43/40 20130101; A01N
43/90 20130101; A01N 43/90 20130101; A01N 43/90 20130101 |
International
Class: |
A01N 43/40 20060101
A01N043/40; A01N 43/42 20060101 A01N043/42; A01N 43/90 20060101
A01N043/90 |
Claims
1. A herbicidal tank mix composition comprising a herbicidally
effective amount of: (a) a compound of the formula (I) ##STR00008##
or an agriculturally acceptable salt or ester thereof, (b)
florasulam or an agriculturally acceptable salt thereof, and (c)
pyroxsulam or an agriculturally acceptable salt thereof.
2. The composition of claim 1, wherein (a) is a C.sub.1-C.sub.4
alkyl or benzyl ester of compound (I).
3. The composition of claim 3, wherein (a) is a methyl ester of
compound (I).
4. The composition of claim 1, wherein (a) is the carboxylic acid
of formula (I).
5. The composition of claim 1, wherein (a) is the methyl ester of
the compound of formula (I) and (b) is florasulam.
6. The composition of any of claims 1-5, wherein the weight ratio
of (a)+(b) to (c) is from about 1:100 to about 100:1.
7. The composition of claim 6, wherein the weight ratio of (a)+(b)
to (c) is from about from about 1:12.5 to about 12.5:1
8. The composition of claim 7, wherein the weight ratio of (a)+(b)
to (c) is from about 1:3.1 to about 1.5:1.
9. The composition of any of claims 1-5, wherein the weight ratio
of (a) to (b) to (c) is from about 1-80 of (a) to about 1-120 of
(b) to about 1-200 of (c).
10. The composition of claim 9, wherein the weight ratio of (a) to
(b) to (c) is from about 1-10 of (a) to about 1-15 of (b) to about
1-25 of (c).
11. The composition of claim 10, wherein the weight ratio of (a) to
(b) to (c) is from about 1-2 of (a) to about 1-2.1 of (b) to about
1-4 of (c).
12. The composition of any of claims 1-11, further comprising a
herbicidally effective amount of an additional herbicide.
13. The composition of claim 12, wherein the additional herbicide
is amidosulfuron, aminopyralid, benfluralin, bicyclopyrone,
bifenox, bromoxynil, carfentrazone, carfentrazone-ethyl,
chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl,
clodinafop-propargyl, clopyralid, difenzoquat, diflufenican,
ethalfluralin, fenoxaprop, fenoxaprop-P-ethyl,
fenoxaprop-P-ethyl+isoxadifen-ethyl, flucarbazone, flufenacet,
flumetsulam, flumioxazin, fluoroglycofen, flupyrsulfuron,
fluroxypyr, flurtamone, fluthiacet, glufosinate, glyphosate,
imazamethabenz, imazamox, indanofan, indaziflam, iodosulfuron,
iodosulfuron-ethyl-sodium, ioxynil, isoproturon, isoxaben, MCPA
esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P,
mesosulfuron, metosulam, metribuzin, metsulfuron,
metsulfuron-methyl, oxyfluorfen, paraflufen-ethyl, paraquat,
pendimethalin, penoxsulam, picloram, picolinafen, pinoxaden,
propoxycarbazone, propyzamide, prosulfocarb, pyraflufen,
pyraflufen-ethyl, pyrasulfotole, pyroxasulfone, rimsulfuron,
saflufenacil, sulfosulfuron, thiencarbazone-methyl, thifensulfuron,
thifensulfuron-methyl, topramezone, tralkoxydim, tri-allate,
triasulfuron, tribenuron, tribenuron-methyl, triclopyr, triclopyr
choline salt, triclopyr esters and salts, trifluralin,
tritosulfuron, benzyl
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-
-carboxylate, and salts, choline salts, esters, optically active
isomers and mixtures thereof.
14. The composition of any of claims 1-13, further comprising a
herbicide safener.
15. The composition of claim 14, wherein the herbicide safener is
cloquintocet (mexyl).
16. The composition of any of claims 1-15, further comprising an
agriculturally acceptable adjuvant.
17. The composition of any of claims 1-16, wherein the composition
is synergistic or exhibits synergy as determined by the Colby
equation.
18. A method of controlling undesirable vegetation comprising
contacting undesirable vegetation or the locus thereof, or foliage,
water or soil, with the composition of any of claims 1-17.
19. The method of claim 18, wherein the composition is applied
post-emergence to the undesirable vegetation.
20. The method of claim 18, wherein the composition is applied
pre-emergence to the undesirable vegetation.
21. The method of claim 18, wherein the undesirable vegetation is
contacted prior to planting a crop.
22. The method of any of claims 18-21, wherein the weight ratio of
(a)+(b) to (c) is from about 1:100 to about 100:1.
23. The method of claim 22, wherein the weight ratio of (a)+(b) to
(c) is from about 1:12.5 to about 12.5:1.
24. The method of claim 23, wherein the weight ratio of (a)+(b) to
(c) is from about 1:3.1 to about 1.5:1.
25. The method of any of claims 18-21, wherein the weight ratio of
(a) to (b) to (c) is from about 1-80 of (a) to about 1-120 of (b)
to about 1-200 of (c).
26. The method of claim 25, wherein the weight ratio of (a) to (b)
to (c) is from about 1-10 of (a) to about 1-15 of (b) to about 1-25
of (c).
27. The method of claim 26, wherein the weight ratio of (a) to (b)
to (c) is from about 1-2 of (a) to about 1-2.1 of (b) to about 1-4
of (c).
28. The method of any of claims 18-27, further comprising
contacting the undesirable vegetation with a herbicidally effective
amount of an additional herbicide.
29. The method of claim 28, wherein the additional herbicide is
amidosulfuron, aminopyralid, benfluralin, bicyclopyrone, bifenox,
bromoxynil, carfentrazone, carfentrazone-ethyl, chlorotoluron,
chlorsulfuron, cinidon, cinidon-ethyl, clodinafop-propargyl,
clopyralid, difenzoquat, diflufenican, ethalfluralin, fenoxaprop,
fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl,
flucarbazone, flufenacet, flumetsulam, flumioxazin, fluoroglycofen,
flupyrsulfuron, fluroxypyr, flurtamone, fluthiacet, glufosinate,
glyphosate, imazamethabenz, imazamox, indanofan, indaziflam,
iodosulfuron, iodosulfuron-ethyl-sodium, ioxynil, isoproturon,
isoxaben, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop,
mecoprop-P, mesosulfuron, metosulam, metribuzin, metsulfuron,
metsulfuron-methyl, oxyfluorfen, paraflufen-ethyl, paraquat,
pendimethalin, penoxsulam, picloram, picolinafen, pinoxaden,
propoxycarbazone, propyzamide, prosulfocarb, pyraflufen,
pyraflufen-ethyl, pyrasulfotole, pyroxasulfone, rimsulfuron,
saflufenacil, sulfosulfuron, thiencarbazone-methyl, thifensulfuron,
thifensulfuron-methyl, topramezone, tralkoxydim, tri-allate,
triasulfuron, tribenuron, tribenuron-methyl, triclopyr, triclopyr
choline salt, triclopyr esters and salts, trifluralin,
tritosulfuron, benzyl
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-
-carboxylate, and salts, choline salts, esters, optically active
isomers and mixtures thereof.
30. The method of any of claims 18-29, wherein (a), (b) and/or (c)
are applied simultaneously.
31. The method of any of claims 18-29, wherein (a), (b) and/or (c)
are applied sequentially.
32. The method of any of claims 18-31, wherein synergy is
determined by the Colby equation.
33. The method of any one of claims 18-32 wherein the undesirable
vegetation is controlled in a crop that is tolerant to glyphosate,
glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins,
aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase)
inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors,
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
protoporphyrinogen oxidase (PPO) inhibitors, triazines, or
bromoxynil.
34. The method of claim 33, wherein the tolerant crop possesses
single or multiple or stacked traits conferring tolerance to single
or multiple herbicides or single or multiple modes of action.
35. The method of any of claims 18-34, wherein the undesirable
vegetation comprises a herbicide resistant or tolerant weed.
36. The method of claim 35, wherein the resistant or tolerant weed
is a biotype with resistance or tolerance to single or multiple
herbicides or single or multiple chemical classes, or inhibitors of
single or multiple herbicide modes of action.
37. The method of claim 36, wherein the resistant or tolerant weed
is a biotype resistant or tolerant to synthetic auxins (2,4-D,
dicamba, MCPA), pyridyloxy auxins, acetolactate synthase (ALS) or
acetohydroxy acid synthase (AHAS) inhibitors, photosystem II
inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, photosystem
I inhibitors, 5-enolpyruvyl-shikimate-3-phosphate (EPSP) synthase
inhibitors, microtubule assembly inhibitors, lipid synthesis
inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid
biosynthesis inhibitors, very long chain fatty acid (VLCFA)
inhibitors, phytoene desaturase (PDS) inhibitors, glutamine
synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD)
inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
herbicides with multiple modes of action, quinclorac,
arylaminopropionic acids, difenzoquat, endothall or
organoarsenicals.
38. The method of any of claims 18-37, wherein the undesirable
vegetation is controlled in annual crop, non-crop, cereal crop,
IVM, range and pasture, tree and vine crops, perennial crop,
fruiting crop, or plantation crop areas, comprising contacting
undesirable vegetation or the locus thereof, or water or soil, in
annual crop, non-crop, cereal crop, IVM, range and pasture, tree
and vine crop, perennial crop, fruiting crop, or plantation crop
areas.
39. The method of claim 38, wherein the undesirable vegetation is
in an annual crop area and the annual crop area is selected from
soybean, corn, cotton, fallow-bed, canola/oilseed rape, sunflower,
sorghum, and cereals (wheat, barley, rice, oats, rye, teff and
triticale).
40. The method of claim 38, wherein the undesirable vegetation is
in a non-crop area and the non-crop area is a pasture, grassland,
rangeland, fallowland, fencerow, parking area, tank farm, storage
area, rights-of-way, utility area, turf, forestry, aquatics,
industrial vegetation management (IVM) or fallow-bed.
41. The method of claim 38 wherein the undesirable vegetation is in
a cereal crop area and the foliage of the cereal crop is not
contacted when the undesirable vegetation is contacted.
42. The method of claim 41, wherein the cereal crop is selected
from rice, wheat, teff, triticale, barley, oats, rye, sorghum,
corn/maize and fallow-bed.
43. The method of claim 38, wherein the undesirable vegetation is
in a perennial crop area and the foliage of the perennial crop is
not contacted when the undesirable vegetation is contacted.
44. The method of claim 43, wherein the perennial crop is a tree
and vine orchard.
45. The method of claim 44, wherein the tree and vine orchard is
selected from citrus, grapes, almond, apple, apricot, avocado,
banana, beechnut, Brazil nut, butternut, cashew, cherry, chestnut,
chinquapin, crab apple, date, feijoa, fig, filbert, hickory nut,
kiwi, lemon, lime, loquat, macadamia nut, mandarin, mango, mayhaws,
oranges, nectarine, olives, peach, pear, pecan, persimmon,
pistachio, plum, pomegranate, prune, quince, tree nut and
walnut.
46. The method of claim 38, wherein the undesirable vegetation is
in a fruiting crop area and the foliage of the fruiting crop is not
contacted when the undesirable vegetation is contacted.
47. The method of claim 46, wherein fruiting crop is selected from
blueberries, guava, papaya, strawberries, taro, blackberries,
pineapple, and raspberries.
48. The method of claim 38, wherein the undesirable vegetation is
in a plantation crop area and the foliage of the plantation crop is
not contacted when the undesirable vegetation is contacted. The
method of claim 48, wherein plantation crop is selected from
coffee, cacao, rubber and palm oil.
Description
BACKGROUND
[0001] The protection of crops from weeds and other vegetation
which inhibit crop growth is a recurring problem in agriculture. To
help combat this problem, a variety of chemicals and chemical
formulations effective in the control of such unwanted vegetation
have been synthesized and evaluated. Different classes of chemical
herbicides have been disclosed in the literature and a large number
are in commercial use. However, there remains a need for improved
compositions and methods of use thereof that are effective in
controlling undesirable vegetation.
SUMMARY
[0002] Provided herein are herbicidal compositions comprising a
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00002##
or an agriculturally acceptable salt or ester thereof, (b)
florasulam or an agriculturally acceptable salt thereof, and (c)
pyroxsulam or an agriculturally acceptable salt thereof. The
compositions may also contain one or more agriculturally acceptable
safeners, adjuvants and/or carriers. In some embodiments, the
mixtures are synergistic or exhibit synergy as determined by the
Colby Equation.
[0003] The three-way mixture can be prepared as a tank mix or
premix. For example, a tank mix or premix containing the compound
of formula (I) or a salt or ester thereof and florasulam or a salt
thereof can bmixed with pyroxsulam or salt thereof to form the
three-component tank mix. In this embodiment, the tank mix,
co-pack, premix or concentrate of the compound of formula (I) and
florasulam and pyroxsulam can be packaged and sold separately, can
be co-packaged together in separate single or multiple containers
or can be formulated together in one package.
[0004] In other embodiments, a premix or concentrate containing the
compound of formula (I) or a salt or ester thereof and pyroxsulam
or a salt thereof can be mixed in a tank or container with
florasulam or a salt thereof to form the tank mix. In this
embodiment, the premix or concentrate of the compound of formula
(I) and pyroxsulam and the florasulam can be packaged and sold
separately, or can be co-packaged together in separate containers,
or can be formulated together in one package.
[0005] In still other embodiments, a premix containing all three
active ingredients can be prepared and sold.
[0006] The ratio of the compound of formula (I) to florasulam in
the premix is from about 1:120 to 80:1; from about 1:15 to 10:1,
and from about 1:2.1 to about 2:1. The ratio of the compound of
formula (I) to florasulam to pyroxsulam in the tank mix or premix
is from about 1-80 to about 1-120 to about 1-200; from about 1-10
to about 1-15 to about 1-25; and from about 1-2 to about 1-2.1 to
about 1-4.
[0007] In another embodiment, methods of controlling undesirable
vegetation in cereal crops (wheat, barley, oats, rye, teff,
triticale and rice), corn/maize, sorghum, sunflower, soybean,
cotton, non-crop (turf, tree and ornamentals), fallow, fallow-bed,
range and pasture, forestry, perennial crops, tree and vine crops
(vineyards, olive, citrus, tree nut (almond, walnut, pecan or
pistachio), pome and stone, fruiting crops, or plantation crop
(palm oil, rubber, coffee or cacao) areas including contacting the
undesirable vegetation or the locus thereof, including but not
limited to foliage, soil or water, with a composition containing a
herbicidally effective amount of (a) a compound of formula (I) or
an agriculturally acceptable ester or salt thereof, (b) florasulam
or an agriculturally acceptable salt thereof, and (c) pyroxsulam or
an agriculturally acceptable salt thereof are described herein. In
some embodiments, the mixtures are synergistic or exhibit synergy
as determined by the Colby Equation.
DETAILED DESCRIPTION
I. Definitions
[0008] As used herein, control of or controlling undesirable
vegetation means killing or preventing the growth of the
vegetation, or causing some other adversely modifying effect to the
vegetation e.g., necrosis, chlorosis, stunting, deviations from
natural growth or development, regulation, desiccation,
retardation, and the like.
[0009] As used herein, herbicide and herbicidal active ingredient
mean a compound that controls undesirable vegetation when applied
in an appropriate amount.
[0010] As used herein, a herbicidally effective or vegetation
controlling amount is an amount of herbicidal active ingredient the
application of which controls the relevant undesirable
vegetation.
[0011] As used herein, applying a herbicide or herbicidal
composition means delivering it directly to the targeted vegetation
or to the locus thereof or to the area where control of undesired
vegetation is desired. Methods of application include, but are not
limited to pre-emergence, post-emergence, foliar, soil, and
in-water applications. Described herein are methods of controlling
undesirable vegetation by applying certain herbicide combinations
or compositions.
[0012] As used herein, plants and vegetation include, but are not
limited to, dormant seeds, germinant seeds, emerging seedlings,
plants emerging from vegetative propagules, immature vegetation,
mature vegetation, reproductive vegetation and established
vegetation.
[0013] As used herein, immature vegetation refers to small
vegetative plants prior to reproductive stage, and mature
vegetation refers to vegetative plants during and after
reproductive stage.
[0014] As used herein, herbicide tolerant cereals (wheat, barley,
oats, teff, rye and rice), corn or sorghum refer to crops that are
genetically modified to be tolerant to various herbicides,
including cereal crops that are genetically modified to be tolerant
to acetolactate synthase (ALS), acetyl CoA carboxylase (ACCase),
2,4-D, dicamba, HPPD, PPO, glyphosate and glufosinate mode of
action herbicides. Examples of 2,4-D tolerant cereals, corn or
sorghum include crops containing the aad-1 gene which confers
tolerance to 2,4-D (U.S. Pat. No. 7,838,733 B2).
[0015] As used herein, glyphosate tolerance refers to cereals
(wheat, barley, oats, teff, rye and rice), corn or sorghum that are
genetically modified to be tolerant to glyphosate. Glyphosate
tolerance can be provided, for example, by the CP4 gene (U.S. Pat.
No. 5,627,061 A) or 2mEPSPS (U.S. Pat. No. 6,566,587 B1) as shown
herein; however, glyphosate tolerance could also be conferred
within the scope of glyphosate-, 2,4-D-, and
glufosinate-tolerant-cereals (wheat, barley, oats, teff, rye and
rice), corn or sorghum described herein by other genes providing
transgenic crop tolerance to glyphosate [e.g., AroA and other Class
II EPSPS (U.S. Pat. No. 7,893,234 B2); GLG23 and other Class III
EPSPS (U.S. Pat. No. 7,700,842 B2); GAT (U.S. Pat. No. 7,405,074
B2), Gox (U.S. Pat. No. 5,463,175 A), or other
glyphosate-metabolism gene; or DGT-28 or other Class IV EPSPS (U.S.
Patent Application Publication 20130217577A1)] and are considered
to be included within the scope of the 2,4-D-, glyphosate- and
glufosinate-tolerant cereals (wheat, barley, oats, teff, rye and
rice), corn or sorghum described herein.
[0016] As used herein, glufosinate tolerance refers to cereals
(wheat, barley, oats, teff, rye and rice), corn or sorghum that are
genetically modified to be tolerant to glufosinate. Glufosinate
tolerance can be provided, for example, by the pat gene (U.S. Pat.
No. 5,276,268 B2) as shown herein; however, glufosinate tolerance
could also be conferred within the scope of the 2,4-D- and
glufosinate-tolerant cereals (wheat, barley, oats, teff, rye and
rice), corn or sorghum described herein by other genes providing
transgenic crop tolerance to glufosinate [e.g., bar (U.S. Pat. No.
5,561,236 A) and dsm2 (PCT International Application
WO2008070845)].
II. Mixtures
[0017] Compositions containing the compound of formula (I) or a
salt or ester thereof, florasulam or a salt thereof, and pyroxsulam
or a salt thereof are described herein. The composition can be in
the form of a tank mix, premix, co-pack or a tank mix of one or
more compositions mixed with one or more separate compositions
containing the compound of formula (I) or a salt or ester thereof,
florasulam or a salt thereof, and pyroxsulam or a salt thereof. The
tank mix can be prepared by mixing a premix, co-pack or tank mix or
concentrate containing the compound of formula (I) and florasulam
or pyroxsulam. Agriculturally acceptable salts and esters refer to
salts and esters that exhibit herbicidal activity, or that are or
can be converted in plants, water, or soil to the referenced
herbicide. Exemplary agriculturally acceptable esters are those
that are or can by hydrolyzed, oxidized, metabolized, or otherwise
converted, e.g., in plants, water, or soil, to the corresponding
carboxylic acid which, depending on the pH, may be in the
dissociated or undissociated form. Exemplary salts include those
derived from alkali or alkaline earth metals and those derived from
ammonia and amines Exemplary cations include sodium, potassium,
magnesium, and ammonium cations of the formula:
R.sup.1R.sup.2R.sup.3R.sup.4N.sup.+
wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each, independently
represents hydrogen or C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12
alkenyl or C.sub.3-C.sub.12 alkynyl, each of which is optionally
substituted by one or more hydroxy, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 alkylthio or phenyl groups, provided that R.sup.1,
R.sup.2, R.sup.3 and R.sup.4 are sterically compatible.
Additionally, any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4
together may represent an aliphatic difunctional moiety containing
one to twelve carbon atoms and up to two oxygen or sulfur atoms.
Salts can be prepared by treatment with a metal hydroxide, such as
sodium hydroxide, with an amine, such as ammonia, trimethylamine,
diethanolamine, 2-methylthiopropylamine, bisallylamine,
2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine
or with a tetraalkylammonium hydroxide, such as tetramethylammonium
hydroxide or choline hydroxide.
[0018] Exemplary esters include those derived from C.sub.1-C.sub.12
alkyl, C.sub.3-C.sub.12 alkenyl, C.sub.3-C.sub.12 alkynyl or
C.sub.7-C.sub.10 aryl-substituted alkyl alcohols, such as methyl
alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol,
butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol,
cyclohexanol or unsubstituted or substituted benzyl alcohols.
Benzyl alcohols may be substituted with from 1-3 substituents
independently selected from halogen, C.sub.1-C.sub.4 alkyl or
C.sub.1-C.sub.4 alkoxy. Esters can be prepared by coupling of the
acids with the alcohol using any number of suitable activating
agents such as those used for peptide couplings such as
dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by
reacting the acids with alkylating agents such as alkylhalides or
alkylsulfonates in the presence of a base such as triethylamine or
lithium carbonate; by reacting the corresponding acid chloride of
an acid with an appropriate alcohol; by reacting the corresponding
acid with an appropriate alcohol in the presence of an acid
catalyst or by transesterification.
[0019] Weight ratios of mixtures are calculated using the acid
equivalent weight(s) of any compounds in the mixture that are salts
or esters. Weight ratios are expressed in units of weight to weight
(grams (g) to g), grams acid equivalent per hectare (g ae/ha) to g
ae/ha), grams acid equivalent per hectare (g ae/ha) to grams active
ingredient per hectare (g ai/ha), or grams active ingredient per
hectare (g ai/ha) to g ai/ha).
[0020] The combination of the compound of formula (I) or
agriculturally acceptable salt or ester thereof, florasulam or
agriculturally acceptable salt thereof, and pyroxsulam or
agriculturally acceptable salt thereof can exhibit synergism, i.e.,
the herbicidal active ingredients are more effective in combination
than when applied individually. As defined in the Herbicide
Handbook of the Weed Science Society of America, Tenth Edition,
2014, p. 487, "`Synergism [is] an interaction of two or more
factors such that the effect when combined is greater than the
predicted effect based on the response of each factor applied
separately." In certain embodiments, the compositions exhibit
synergy as determined by Colby's equation as described in Colby, S.
R. Calculation of the synergistic and antagonistic response of
herbicide combinations. Weeds 1967, 15, 20-22.
[0021] A. Halauxifen
[0022] The compound of formula (I) has the following structure:
##STR00003##
The compound of formula (I) can be identified by the name
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxyl-
ic acid and and has been described in U.S. Pat. No. 7,314,849 (B2),
which is incorporated herein by reference in its entirety. It is
also referred to as halauxifen. The methyl ester is known as
halauxifen-methyl and is sold commercially as ARYLEX.RTM.
active.
[0023] In certain embodiments of the compositions and methods
described herein, the compound of formula (I), i.e., the carboxylic
acid, is employed. In certain embodiments, a carboxylate salt of
the compound of formula (I) is employed. In certain embodiments, an
arylalkyl or alkyl ester is employed. In certain embodiments, a
benzyl, substituted benzyl, or C.sub.1-C.sub.4 alkyl, e.g., methyl
or n-butyl ester is employed. In certain embodiments, the methyl
ester, benzyl ester, or potassium salt is employed.
[0024] Exemplary uses of of the compound of the formula (I) include
controlling undesirable vegetation, including e.g. grass,
broadleaf, and sedge weeds, in multiple crop and non-crop
situations.
[0025] B. Florasulam
[0026] Florasulam is a triazolopyrimidine sulfonamide having the
structure below:
##STR00004##
[0027] Triazolopyrimidine sulfonamides are a chemical class of
herbicides having a triazolopyrimidine sulfonamide core structure.
Their mode-of-action is believed to involve the inhibition of
acetolactate synthase (ALS), an enzyme common to plants and
microorganisms but not found in animals. Exemplary herbicidal uses
of triazolopyrimidine sulfonamides include, but are not limited to,
use for control of nuisance sedge, broadleaf, and grass weeds in
multiple crops and turf.
[0028] Florasulam is
N-(2,6-difluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-
-2-sulfonamide and has the following structure. Its herbicidal
activity is exemplified in Tomlin, C. D. S., Ed. The Pesticide
Manual: A World Compendium, 15.sup.th ed.; BCPC: Alton, 2009
(hereafter "The Pesticide Manual, Fifteenth Edition, 2009").
Exemplary uses of florasulam include, but are not limited to, its
use as a herbicide in post-emergence control of broadleaf weeds in
cereals, maize and turf.
[0029] C. Pyroxsulam
[0030] Pyroxsulam is is a triazolopyrimidine sulfonamide having the
structure below:
##STR00005##
[0031] Pyroxsulam is
N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(triflu-
oromethyl)-pyridine-3-sulfonamide and possesses the following
structure. Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Exemplary uses of pyroxsulam
include its use as a herbicide for broad spectrum post-emergence
control of annual grass and broadleaf weeds in cereals.
III. Tank Mixes, Pre-Mixes and Co-Packs
[0032] Tank mixes, pre-mixes and co-packs containing the compound
of formula (I) or a salt or ester thereof, florasulam or a salt
thereof, and pyroxsulam or a salt thereof are described herein. In
some embodiments, the tank mix is prepared by mixing a premix of
the compound of formula (I) or a salt or ester thereof and
florasulam or a salt thereof with a concentrate containing
pyroxsulam or a salt thereof. In other embodiments, the tank mix is
prepared by mixing the compound of formula (I) or a salt or ester
thereof and pyroxsulam or a salt thereof with florsulam or a salt
thereof. In still other embodiments, the premix or co-pack contains
all three active ingredients which is diluted prior to
use/application. The premix or suitable pre-mixes can contain one
or more suitable adjuvants, safeners and/or carriers.
[0033] In some embodiments, compositions provided herein further
comprise at least one agriculturally acceptable adjuvant or
carrier. Suitable adjuvants or carriers should not be phytotoxic to
valuable crops, particularly at the concentrations employed in
applying the compositions for selective weed control in the
presence of crops, and should not react chemically with herbicidal
components or other composition ingredients. Such mixtures can be
designed for application directly to weeds or their locus or can be
concentrates or formulations that are normally diluted with
additional carriers and adjuvants before application. They can be
solids, such as, for example, dusts, granules, water-dispersible
granules, microcapsules or wettable powders, or liquids, such as,
for example, emulsifiable concentrates, solutions, emulsions or
suspensions. They can also be provided as a pre-mix or tank
mixed.
[0034] Suitable agricultural adjuvants and carriers include, but
are not limited to, crop oil concentrate; nonylphenol ethoxylate;
benzylcocoalkyldimethyl quaternary ammonium salt; blend of
petroleum hydrocarbon, alkyl esters, organic acid, and anionic
surfactant; C.sub.9-C.sub.11 alkylpolyglycoside; phosphated alcohol
ethoxylate; natural primary alcohol (C.sub.12-C.sub.16) ethoxylate;
di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;
nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated
seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow
amine ethoxylate (15 EO); PEG(400) dioleate-99.
[0035] Liquid carriers that can be employed include water and
organic solvents. The organic solvents include, but are not limited
to, petroleum fractions or hydrocarbons such as mineral oil,
aromatic solvents, paraffinic oils, and the like; vegetable oils
such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower
seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm
oil, peanut oil, safflower oil, sesame oil, tung oil and the like;
esters of the above vegetable oils; esters of monoalcohols or
dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy
containing), such as 2-ethyl hexyl stearate, n-butyl oleate,
isopropyl myristate, propylene glycol dioleate, di-octyl succinate,
di-butyl adipate, di-octyl phthalate and the like; esters of mono,
di and polycarboxylic acids and the like. Specific organic solvents
include, but are not limited to toluene, xylene, petroleum naphtha,
crop oil, acetone, methyl ethyl ketone, cyclohexanone,
trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate,
butyl acetate, propylene glycol monomethyl ether and diethylene
glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl
alcohol, amyl alcohol, ethylene glycol, propylene glycol,
glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides,
dimethyl sulfoxide, liquid fertilizers and the like. In certain
embodiments, water is the carrier for the dilution of
concentrates.
[0036] Suitable solid carriers include but are not limited to talc,
pyrophyllite clay, silica, attapulgus clay, kaolin clay,
kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate,
bentonite clay, Fuller's earth, cottonseed hulls, wheat flour,
soybean flour, pumice, wood flour, walnut shell flour, lignin,
cellulose, and the like.
[0037] In some embodiments, the compositions described herein
further comprise one or more surface-active agents. In some
embodiments, such surface-active agents are employed in both solid
and liquid compositions, and in certain embodiments those designed
to be diluted with carrier before application. The surface-active
agents can be anionic, cationic or nonionic in character and can be
employed as emulsifying agents, wetting agents, suspending agents,
or for other purposes. Surfactants which may also be used in the
present formulations are described, inter alia, in McCutcheon's
Detergents and Emulsifiers Annual, MC Publishing Corporation:
Ridgewood, N J, 1998 and in Encyclopedia of Surfactants, Vol.
I-III, Chemical Publishing Company: New York, 1980-81.
Surface-active agents include, but are not limited to salts of
alkyl sulfates, such as diethanolammonium lauryl sulfate;
alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate;
alkylphenol-alkylene oxide addition products, such as
nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition
products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such
as sodium stearate; alkyl-naphthalene-sulfonate salts, such as
sodium dibutylnaphthalenesulfonate; dialkyl esters of
sulfosuccinate salts, such as sodium di(2-ethylhexyl)
sulfosuccinate; sorbitol esters, such as sorbitol oleate;
quaternary amines, such as lauryl trimethylammonium chloride;
polyethylene glycol esters of fatty acids, such as polyethylene
glycol stearate; block copolymers of ethylene oxide and propylene
oxide; salts of mono and dialkyl phosphate esters; vegetable or
seed oils such as soybean oil, rapeseed/canola oil, olive oil,
castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed
oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil,
tung oil and the like; and esters of the above vegetable oils, and
in certain embodiments, methyl esters.
[0038] In some embodiments, these materials, such as vegetable or
seed oils and their esters, can be used interchangeably as an
agricultural adjuvant, as a liquid carrier or as a surface active
agent.
[0039] Other exemplary additives for use in the compositions
provided herein include but are not limited to compatibilizing
agents, antifoam agents, sequestering agents, neutralizing agents
and buffers, corrosion inhibitors, dyes, odorants, spreading
agents, penetration aids, sticking agents, dispersing agents,
thickening agents, freezing point depressants, antimicrobial
agents, and the like. The compositions may also contain other
compatible components, for example, other herbicides, plant growth
regulants, fungicides, insecticides, and the like and can be
formulated with liquid fertilizers or solid, particulate fertilizer
carriers such as ammonium nitrate, urea and the like.
[0040] The tank mixes described herein can further contain one or
more additional herbicides. The herbicides can be incorporated into
the one or more of the pre-mixes, tank mixes or concentrates or can
be added at the time the tank mix is prepared by formulation or
prior to application. When used in conjunction with other
herbicides, the composition can be formulated with the other
herbicide or herbicides, tank-mixed with the other herbicide or
herbicides or applied sequentially with the other herbicide or
herbicides. Some of the herbicides that can be employed in
conjunction with the compositions and methods described herein
include, but are not limited to acid, salt and ester forms of the
following herbicides: 4-CPA, 4-CPB, 4-CPP, 3,4-DA, 2,4-D esters and
salts, 2,4-DB, 3,4-DB, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB,
acetochlor, acifluorfen, aclonifen, acrolein, alachlor,
allidochlor, alloxydim, allyl alcohol, alorac, ametridione,
ametryn, amibuzin, amicarbazone, amidosulfuron,
aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole,
ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine,
azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid,
benazolin, bencarbazone, benfluralin, benfuresate,
bensulfuron-methyl, bensulide, bentazon, benthiocarb, benzadox,
benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor,
benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos,
bispyribac-sodium, borax, bromacil, bromobonil, bromobutide,
bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil,
butamifos, butenachlor, buthidazole, buthiuron, butralin,
butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium
chlorate, calcium cyanamide, cambendichlor, carbasulam,
carbetamide, carboxazole, chlorprocarb, carfentrazone (e.g.,
carfentrazone-ethyl), CDEA, CEPC, chlomethoxyfen, chloramben,
chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam,
chloreturon, chlorfenac, chlorfenprop, chlorflurazole,
chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon,
chlorotoluron, chloroxuron, chloroxynil, chlorpropham,
chlorsulfuron, chlorthal, chlorthiamid, cinidon (e.g.,
cinidon-ethyl), cinmethylin, cinosulfuron, cisanilide, clethodim,
cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop,
cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper
sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn,
cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim,
cycluron, cyhalofop (e.g., cyhalofop-butyl), cyperquat, cyprazine,
cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor,
desmedipham, desmetryn, di-allate, dicamba, dichlobenil,
dichloralurea, dichlormate, dichlorprop, dichlorprop-P,
diclofop-methyl, diclosulam, diethamquat, diethatyl, difenopenten,
difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron,
dimepiperate, dimethachlor, dimethametryn, dimethenamid,
dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate,
dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn,
diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP,
eglinazine, endothal, epronaz, EPTC, erbon, esprocarb,
ethbenzamide, ethalfluralin, ethametsulfuron, ethidimuron,
ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen,
ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam,
fenoprop, fenoxaprop (e.g., fenoxaprop-P-ethyl),
fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone, fenquinotrione,
fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate,
flamprop, flamprop-M, flazasulfuron, fluazifop (e.g.,
fluazifop-P-butyl), fluazolate, flucarbazone, flucetosulfuron,
fluchloralin, flufenacet, flufenican, flufenpyr (e.g.,
flufenpyr-ethyl), flumetsulam, flumezin, flumiclorac (e.g.,
flumiclorac-pentyl), flumioxazin, flumipropyn, fluometuron,
fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen,
fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron,
fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet,
fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen,
glufosinate, glyphosate, halosafen, halosulfuron (e.g.,
halosulfuron-methyl), haloxydine, haloxyfop-methyl, haloxyfop-P
(e.g., haloxyfop-P-methyl), hexachloroacetone, hexaflurate,
hexazinone, imazamethabenz, imazamox, imazapic, imazapyr,
imazaquin, imazosulfuron, indanofan, indaziflam, iodobonil,
iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium,
iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam,
isocarbamid, isocil, isomethiozin, isonoruron, isopolinate,
isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,
isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen,
lenacil, linuron, MAA, MAMA, MCPA esters and amines,
MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet,
mefluidide, mesoprazine, mesosulfuron, mesotrione, metam,
metamifop, metamitron, metazachlor, metazosulfuron, metflurazon,
methabenzthiazuron, methalpropalin, methazole, methiobencarb,
methiozolin, methiuron, methometon, methoprotryne, methyl bromide,
methyl isothiocyanate, methyldymron, metobenzuron, metobromuron,
metolachlor, metosulam, metoxuron, metribuzin, metsulfuron,
metsulfuron-methyl, molinate, monalide, monisouron,
monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA,
naproanilide, napropamide, napropamide-M, naptalam, neburon,
nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen,
norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene,
orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon,
oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl,
parafluron, paraquat, pebulate, pelargonic acid, pendimethalin,
penoxsulam, pentachlorophenol, pentanochlor, pentoxazone,
perfluidone, pethoxamid, phenisopham, phenmedipham (e.g.,
phenmedipham-ethyl), phenobenzuron, phenylmercury acetate,
picloram, picolinafen, pinoxaden, piperophos, potassium arsenite,
potassium azide, potassium cyanate, pretilachlor, primisulfuron
(e.g., primisulfuron-methyl), procyazine, prodiamine, profluazol,
profluralin, profoxydim, proglinazine, prohexadione-calcium,
prometon, prometryn, propachlor, propanil, propaquizafop,
propazine, propham, propisochlor, propoxycarbazone,
propyrisulfuron, propyzamide, prosulfalin, prosulfocarb,
prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen
(e.g., pyraflufen-ethyl), pyrasulfotole, pyrazogyl, pyrazolynate,
pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb,
pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac,
pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, quinclorac,
quinmerac, quinoclamine, quinonamid, quizalofop,
quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil,
S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron,
simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide,
sodium chlorate, sulcotrione, sulfallate, sulfentrazone,
sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin,
swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione,
tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,
terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron,
thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl,
thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil,
tiocarbazil, tioclorim, topramezone, tolpyralate, tralkoxydim,
triafamone, tri-allate, triasulfuron, triaziflam, tribenuron (e.g.,
tribenuron-methyl), tricamba, triclopyr (e.g., triclopyr choline
salt), triclopyr esters and salts, tridiphane, trietazine,
trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron,
trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan,
tritac tritosulfuron, vernolate, xylachlor, benzyl
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-
-carboxylate and salts, choline salts, esters, optically active
isomers and mixtures thereof.
[0041] In some embodiments, the compositions described herein are
employed in combination with one or more herbicide safeners, such
as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide,
cloquintocet (mexyl), cyometrinil, daimuron, dichlormid,
dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl,
fenclorim, flurazole, fluxofenim, furilazole, harpin proteins,
isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate,
naphthalic anhydride (NA), oxabetrinil, R29148 and
N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
In some embodiments, the safeners are employed in rice, cereal,
corn, or maize settings. In some embodiments, the safener is
cloquintocet or an ester or salt thereof. In certain embodiments,
cloquintocet is utilized to antagonize harmful effects of the
compositions on rice and cereals. In some embodiments, the safener
is cloquintocet (mexyl).
[0042] In some embodiments, the compositions and methods described
herein can be used in combination with one or more seed treatments
known to be employed in the safening of rice and compounds of
formula (I), including naphthalic anhydride and CAS registry number
129531-12-0
(N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),
which has the following structure,
##STR00006##
and CAS registry number 98967-94-3 (methyl
3-((5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine)-2-sulfonamido)thiophene-
-2-carboxylate), which has the following structure,
##STR00007##
[0043] In some embodiments, the concentration of the active
ingredients in the compositions described herein is from about
0.0005 to 98 percent by weight. In some embodiments, the
concentration is from about 0.0006 to 90 percent by weight. In
compositions designed to be employed as concentrates, the active
ingredients, in certain embodiments, are present in a concentration
from about 0.1 to 98 weight percent, and in certain embodiments
about 0.5 to 90 weight percent. Such compositions are, in certain
embodiments, diluted with an inert carrier, such as water, before
application. The diluted compositions usually applied to weeds or
the locus of weeds contain, in certain embodiments, about 0.005 to
99 weight percent active ingredient and in certain embodiments
contain about 0.01 to 25.0 weight percent.
[0044] In some embodiments, the compound of formula (I) or
agriculturally acceptable ester or salt thereof, florasulam, and
pyroxsulam are used in combination with herbicides that are
selective for the crops being treated and which complement the
spectrum of weeds controlled by these compounds at the application
rate employed. In some embodiments, the compositions described
herein and other complementary herbicides are applied at the same
time, either as a combination formulation or as a tank mix, at the
same time or as sequential applications.
[0045] The present compositions can be applied to weeds or their
locus thereof, including but not limited to, foliage or soil by the
use of conventional ground or aerial dusters, sprayers, and granule
applicators, and by other conventional means known to those skilled
in the art.
[0046] Units of weight are expressed in units of weight to weight
(g to g), as g ae/ha (grams acid equivalent/ha) to g ai/ha (grams
active ingredient/ha); such as g ae/ha to g ai/ha; as g ae/ha to g
ae/ha and as g ai/ha to g ai/ha.
[0047] In certain embodiments of the compositions and methods
described herein, (a) the compound of formula (I) or agriculturally
acceptable ester or salt thereof plus (b) florasulam or
agriculturally acceptable salt thereof is used in combination with
(c) pyroxsulam or agriculturally acceptable salt thereof. With
regard to the compositions, in some embodiments, the weight ratio
of (a) the compound of formula (I) or agriculturally acceptable
ester or salt thereof plus (b) florasulam or agriculturally
acceptable salt thereof to (c) pyroxsulam or agriculturally
acceptable salt thereof is within the range from about 1:100 to
about 100:1, from about 1:90 to about 90:1, from about 1:80 to
about 80:1, from about 1:70 to about 70:1, from about 1:60 to about
60:1, from about 1:50 to about 50:1, from about 1:40 to about 40:1,
from about 1:30 to about 30:1, from about 1:20 to about 20:1, from
about 1:18 to about 18:1, from about 1:15 to about 15:1, from about
1:14 to about 14:1, from about 1:13 to about 13:1, and from about
1:12.5 to about 12.5:1. In additional embodiments, the weight ratio
of (a) the compound of formula (I) or agriculturally acceptable
ester or salt thereof plus (b) florasulam or agriculturally
acceptable salt thereof to (c) pyroxsulam or agriculturally
acceptable salt thereof is within the range from about 1:12 to
about 12:1, from about 1:11 to about 11:1, from about 1:10 to about
10:1, from about 1:9 to about 9:1, from about 1:8 to about 8:1,
from about 1:7 to about 7:1, from about 1:6 to about 6:1, from
about 1:5 to about 5:1, from about 1:4 to about 4:1, and from about
1:3.75 to about 3:1. In certain embodiments, the weight ratio of
(a) the compound of formula (I) or agriculturally acceptable ester
or salt thereof plus (b) florasulam or agriculturally acceptable
salt thereof to (c) pyroxsulam or agriculturally acceptable salt
thereof is within the range from about 1:3.5 to about 2:1. In other
embodiments, the weight ratio of (a) the compound of formula (I) or
agriculturally acceptable ester or salt thereof plus (b) florasulam
or agriculturally acceptable salt thereof to (c) pyroxsulam or
agriculturally acceptable salt thereof is within the range from
about 1:3.1 to about 1.5:1.
[0048] In certain embodiments of the compositions and methods
described herein, the combination of herbicidally active
ingredients consists of the three components used in amounts such
that the weight ratio of (a) to (b) to (c) is from about 1-80 of
(a) to about 1-120 of (b) to about 1-200 of (c). In additional
embodiments, the weight ratios of the three components include from
about 1-70 of (a) to about 1-100 of (b) to about 1-180 of (c); from
about 1-60 of (a) to about 1-90 of (b) to about 1-150 of (c); from
about 1-50 of (a) to about 1-80 of (b) to about 1-125 of (c); from
about 1-40 of (a) to about 1-70 of (b) to about 1-100 of (c); from
about 1-30 of (a) to about 1-50 of (b) to about 1-80 of (c); from
about 1-20 of (a) to about 1-40 of (b) to about 1-60 of (c); from
about 1-15 of (a) to about 1-30 of (b) to about 1-40 of (c); from
about 1-12.5 of (a) to about 1-20 of (b) to about 1-30 of (c); from
about 1-11 of (a) to about 1-17.5 of (b) to about 1-27 of (c); and
from about 1-10 of (a) to about 1-15 of (b) to about 1-25 of (c).
In certain embodiments, (a) the compound of formula (I) or
agriculturally acceptable ester or salt thereof, (b) florasulam or
agriculturally acceptable salt thereof, and (c) pyroxsulam or
agriculturally acceptable salt thereof, are used in amounts such
that the weight ratio of (a) to (b) to (c) is from about 1-9 of (a)
to about 1-12 of (b) to about 1-20 of (c); from about 1-8 of (a) to
about 1-10 of (b) to about 1-18 of (c); from about 1-7 of (a) to
about 1-8 of (b) to about 1-15 of (c); from about 1-6 of (a) to
about 1-7 of (b) to about 1-12 of (c); from about 1-5 of (a) to
about 1-6 of (b) to about 1-10 of (c); from about 1-4 of (a) to
about 1-5 of (b) to about 1-8 of (c); and from about 1-3 of (a) to
about 1-4 of (b) to about 1-6 of (c). In other embodiments, (a) the
compound of formula (I) or agriculturally acceptable ester or salt
thereof, (b) florasulam or agriculturally acceptable salt thereof,
and (c) pyroxsulam or agriculturally acceptable salt thereof, are
used in amounts such that the weight ration of (a) to (b) to (c) is
from about 1-2 to about 1-2.1 to about 1-4.
[0049] In the embodiments just described, the weight ratio of (a)
the compound of formula (I) or agriculturally acceptable ester or
salt thereof to (b) florasulam or agriculturally acceptable salt
thereof [i.e. (a):(b)] can be further defined such that the weight
ratio of (a) to (b) is from about 1:120 to about 80:1. In
additional embodiments, the weight ratio of the two components
include from about 1:100 to about 75:1; from about 1:90 to about
1:70; from about 1:80 to about 75:1; from about 1:70 to about 70:1;
from about 1:60 to about 60:1; from about 1:50 to about 50:1; from
about 1:35 to about 35:1; from about 1:25 to about 25:1; from about
1:20 to about 20:1; from about 1:17 to about 17:1; from about 1:16
to about 15:1; and from about 1:15 to about 10:1. In additional
embodiments, the weight ratio of the two components include from
about 1:12 to about 8:1; from about 1:10 to about 7.5:1; from about
1:8 to about 7:1; from about 1:6 to about 6:1; from about 1:5 to
about 5:1; from about 1:4 to about 4:1; from about 1:3 to about
3:1; from about 1:2.5 to about 2.5:1; and from about 1:2.1 to about
2:1.
[0050] With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation with a
composition described herein, e.g., sequentially or simultaneously.
In some embodiments, the composition is applied at an application
rate from about 1.00 grams active ingredient per hectare (g ai/ha)
to about 100 g ai/ha based on the total amount of active
ingredients in the composition. In certain embodiments, the
composition is applied at an application rate from about 4 g ai/ha
to about 50 g ai/ha based on the total amount of active ingredients
in the composition. In certain embodiments, the composition is
applied at an application rate from about 10 g ai/ha to about 40 g
ai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate from about 15.6 g ai/ha to about 31 g ai/ha
based on the total amount of active ingredients in the
composition.
[0051] The components of the mixtures described herein can be
applied either separately, sequentially, tank-mixed or as part of a
multipart herbicidal system. In some embodiments, all three
components may be formulated together (e.g., in the same
formulation) or separately (e.g., in separate formulations) and
applied simultaneously. Alternatively, two of the three components
can be formulated together (e.g., the compound of formula (I) or
agriculturally acceptable ester or salt thereof and florasulam or
agriculturally acceptable salt thereof) and the third component
(pyroxsulam or agriculturally acceptable salt thereof) formulated
separately and the two formulations applied simultaneously. In
another embodiment, one or more components may be formulated
separately and the components applied sequentially or in a tank
mix. For example, each component can be formulated separately and
the three components applied sequentially or in a tank mix.
Alternatively, two of the three components can be formulated
together (e.g., the compound of formula (I) or agriculturally
acceptable ester or salt thereof and florasulam or agriculturally
acceptable salt thereof) and the third component (pyroxsulam or
agriculturally acceptable salt thereof) formulated separately and
the two formulations applied sequentially or in a tank mix.
Alternatively, two of the three components can be formulated
together (e.g., the compound of formula (I) or agriculturally
acceptable ester or salt thereof and pyroxsulam or agriculturally
acceptable salt thereof) and the third component (florasulam or
agriculturally acceptable salt thereof) formulated separately and
the two formulations applied sequentially or in a tank mix. The
time period between applications can vary, for example 0.0001,
0.001, 0.01, 0.1, 0.25, 0.5, 1, 2, 4, 6, 8, 10, or 12 hours or
longer or 1, 2, 3, 4, 5, 6, or 7 days or longer.
[0052] In one embodiment, the compositions exhibit synergy against
a variety of weed types. In one embodiment, the combination of the
compound of formula (I) or agriculturally acceptable ester or salt
thereof plus florasulam or agriculturally acceptable salt thereof
to pyroxsulam or agriculturally acceptable salt thereof in a ratio
of about 1:2.9 to about 1.2:1 exhibits greater than about 3, 4, 5,
6, 7, 8, 9, 10, 11, 12, 13, 15, 18, 20, 22, 25, 28, 29, 30, 35, 37,
39, or 40% control compared to the Colby predicted value at 14-78
days after application (DAA).
[0053] In one embodiment, the compositions exhibit synergy against
a variety of weed types. In one embodiment, the combination of the
compound of formula (I) or agriculturally acceptable ester or salt
thereof to florasulam or agriculturally acceptable salt thereof to
pyroxsulam or agriculturally acceptable salt thereof in a ratio of
about 1:2.1:6.25 to about 1:0.63:2 exhibits greater than about 4,
5, 6, 7, 8, 9, 10, 11, 12, 15, 16, 17, 18, 20, 22, 23, 25, 28, 30,
33, 35, 37, 39, 40, 45, 48, 50, 52, or 55% control compared to the
Colby predicted value at 14-84 days after application (DAA).
[0054] In another embodiment, the compositions exhibit synergy as
defined by the efficacy values defined above against a variety of
weed types or crops, including but not limited to, Agropyron repens
L. (quackgrass, AGRRE), Alopecurus myosuroides Huds. (blackgrass,
ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Centaurea
cyanus (cornflower, CENCY), Consolida regalis S. F. Gray (branching
larkspur, CNSRE), Echinochloa crus-galli (L.) P. Beauv.
(barnyardgrass, ECHCG), Galium aparine L. (catchweed bedstraw,
GALAP), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria
recutita L. (wild chamomile, MATCH), Matricaria inodora (scentless
mayweed, MATIN), Solanum nigrum L. (black nightshade, SOLNI),
Stellaria media (L.) Vill. (common chickweed, STEME), and Viola
arvensis Murr. (field violet, VIOAR).
[0055] In another embodiment, the compositions exhibit synergy as
defined by the efficacy values defined above against a variety of
weed types or crops, including but not limited to, Avena sp. (oats,
AVESS), Avena macrocarpa Moench (wild red oat, AVEST), Lamium
purpureum L. (purple deadnettle, LAMPU), Lolium multiflorum Lam.
(Italian ryegrass, LOLMU), Lolium rigidum (rigid ryegrass, LOLRI),
Lolium L. sp. (ryegrass, LOLSS), Papaver rhoeas L. (common poppy,
PAPRH), Solanum nigrum L. (black nightshade, SOLNI), and Stellaria
media (L.) Vill. (common chickweed, STEME).
[0056] In another embodiment, the compositions can be used to
control glyphosate-tolerant soybeans (GLXMA), cotton (GOSHI),
sunflower (HELAN) and other crops that have single site tolerance
to, including but not limited to, glyphosate, ALS, ACCase,
glufosinate, and other herbicide modes of action.
IV. Methods of Use
[0057] Herbicidal activity (control of undesirable vegetation in a
crop or non-crop situation) is exhibited by the herbicidal
compositions when they are applied pre- and post-emergence directly
to the plant or to the locus of the plant at any stage of growth,
or to the area where control of vegetation is desired. The effect
observed depends upon the plant species to be controlled, the stage
of growth of the plant, the application parameters of dilution and
spray drop size, the particle size of solid components, the
environmental conditions at the time of use, the specific compound
employed, the specific adjuvants and carriers employed, the soil
type, and the like, as well as the amount of chemical applied.
These and other factors can be adjusted to promote non-selective or
selective herbicidal action. In some embodiments, the compositions
described herein are applied as a post-emergence application to the
crop and undesirable vegetation, pre-emergence application to the
crop and post-emergence to the undesirable vegetation, and as
multiple post-emergence applications to relatively immature and
mature undesirable vegetation to achieve the maximum control of
weeds.
[0058] In some embodiments, methods of controlling undesirable
vegetation in non-crop, perennial crop, fruiting crop, or
plantation crop areas, comprising contacting undesirable vegetation
or the locus thereof, including but not limited to foliage, soil or
water, with a composition containing a mixture containing
herbicidally effective amounts of (a) the compound of formula (I)
or agriculturally acceptable ester or salt thereof, (b) florasulam
or agriculturally acceptable salt thereof, and (c) pyroxsulam or
agriculturally acceptable salt thereof are described herein. In
certain embodiments, the methods employ the compositions described
herein.
[0059] The compositions and methods provided herein are utilized to
control undesirable vegetation. Undesirable vegetation includes,
but is not limited to, undesirable vegetation that occurs in
oilseed rape/canola, vegetables, Brassica spp, ornamentals, cereal
crops, including but not limited to rice, wheat, teff, triticale,
barley, oats, rye, sorghum, and corn/maize; row crops, fallow-bed,
sunflower, sugarcane, non-crop areas, including but not limited to
pastures, grasslands, rangelands, fallowland, fencerows, parking
areas, tank farms, storage areas, rights-of-way, utility areas,
turf, forestry, aquatics, industrial vegetation management (IVM)
and fallow-bed prior to planting crops; perennial crops where the
application contacts the undesirable vegetation but does not
contact the crop foliage, such as tree and vine orchards, including
but not limited to citrus, grapes, almond, apple, apricot, avocado,
banana, beechnut, Brazil nut, butternut, cashew, cherry, chestnut,
chinquapin, crab apple, date, feijoa, fig, filbert, hickory nut,
kiwi, lemon, lime, loquat, macadamia nut, mandarin, mango, mayhaw,
nectarine, olive, oranges, peach, pear, pecan, persimmon,
pistachio, plum, pome fruit, pomegranate, prune, quince, stone
fruit, tree nuts and walnut; fruiting crops (e.g., blueberries,
guava, papaya, pineapple, strawberries, taro, blackberries and
raspberries); and plantation crops (including, but not limited to,
coffee, cacao, rubber and palm oil).
[0060] The compositions and methods provided herein are utilized to
control undesirable vegetation. Undesirable vegetation includes,
but is not limited to, undesirable vegetation that occurs in annual
crops such as 2,4-D-, ALS-, ACCase-, glyphosate- and
glufosinate-tolerant cereal crops, including but not limited to
rice, wheat, barley, oats, teff, rye and sorghum.
[0061] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in oilseed rape, canola,
drilled crops and cereal crops. In certain embodiments, the
undesirable vegetation is Agropyron repens L. (quackgrass, AGRRE),
Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti
(L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA),
Avena sp. (oats, AVESS), Avena macrocarpa Moench (wild red oat,
AVEST), Bromus tectorum L. (downy brome, BROTE), Centaurea cyanus
(cornflower, CENCY), Consolida regalis S. F. Gray (branching
larkspur, CNSRE), Lolium multiflorum Lam. (Italian ryegrass,
LOLMU), Lolium rigidum (rigid ryegrass, LOLRI), Lolium multiflorum
subsp. Gaudini (annual ryegrass, LOLMG), Matricaria inodora
(scentless mayweed, MATIN), Phalaris minor Retz. (littleseed
canarygrass, PHAMI), Poa annua L. (annual bluegrass, POAAN),
Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail,
SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Cirsium
arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L.
(catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia,
KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Lolium L.
sp. (ryegrass, LOLSS), Matricaria recutita L. (wild chamomile,
MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed,
MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum
convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian
thistle, SASKR), Solanum nigrum L. (black nightshade, SOLNI),
Stellaria media (L.) Vill. (common chickweed, STEME), Veronica
persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr.
(field violet, VIOAR), or Viola tricolor L. (wild violet,
VIOTR).
[0062] In some embodiments, the compositions and methods provided
herein are utilized to control undesirable vegetation in rice. In
certain embodiments, the undesirable vegetation is Brachiaria
platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP),
Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA),
Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG),
Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa
oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa
oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Ischaemum
rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.)
Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.)
Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.)
Hitchc. (Amazon sprangletop, LEFPA), Panicum dichotomiflorum (L.)
Michx. (Fall panicum, PANDI), Paspalum dilatatum Poir.
(dallisgrass, PASDI), Cyperus difformis L. (smallflower flatsedge,
CYPDI), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus
iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple
nutsedge, CYPRO), Eleocharis species (ELOSS), Fimbristylis miliacea
(L.) Vahl (globe fringerush, FIMMI), Schoenoplectus juncoides Roxb.
(Japanese bulrush, SCPJU), Schoenoplectus maritimus L. (sea
clubrush, SCPMA), Schoenoplectus mucronatus L. (ricefield bulrush,
SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera
philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma
plantago-aquatica L. (common water plantain, ALSPA), Amaranthus
species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb.
(redstem, AMMCO), Eclipta alba (L.) Hassk. (American false daisy,
ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI),
Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE),
Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE),
Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU),
Monochoria korsakowii Regel & Maack (monochoria, MOOKA),
Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria,
MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU),
Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY),
Polygonum persicaria L. (ladysthumb, POLPE), Polygonum
hydropiperoides Michx. (mild smartweed, POLHP), Rotala indica
(Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species,
(arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill
(hemp sesbania, SEBEX), Solanum nigrum L. (black nightshade,
SOLNI), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
[0063] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation found in tree and vine
crops, perennial crops, IVM and non-crop areas. In certain
embodiments, the undesirable vegetation is Alopecurus myosuroides
Huds. (blackgrass, ALOMY), Amaranthus palmeri S. Wats. (Palmer
amaranth, AMAPA), Avena fatua L. (wild oat, AVEFA), Brachiaria
decumbens Stapf. or Urochloa decumbens (Stapf) R. D. Webster
(Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.)
Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R. D. (beard
grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa
platyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),
Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea
(Link) R. D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L.
(southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican
crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman
(sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large
crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv.
(barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice,
ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium
multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum
Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso
millet, PANMI), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp
sesbania, SEBEX), Setaria faberi Herrm. (giant foxtail, SETFA),
Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum
halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.)
Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus
L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge,
CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus
species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L.
(common ragweed, AMBEL), Ambrosia psilostachya DC. (western
ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda
cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca
L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks,
BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC.,
Spermacoce alata Aubl. or Spermacoce latifolia (broadleaf
buttonweed, BOILF), Chenopodium album L. (common lambsquarters,
CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR),
Commelina benghalensis L. (tropical spiderwort, COMBE), Datura
stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot,
DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL),
Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge,
EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron
bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane,
ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq.
(horseweed, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall
fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN),
Jacquemontia tamnifolia (L.) Griseb. (smallflower morningglory,
IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE),
Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola
L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (common
purslane, POROL), Richardia species (pusley, RCHSS), Salsola tragus
L. (Russian thistle, SASKR), Sida species (sida, SIDSS), Sida
spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild
mustard, SINAR), Solanum ptychanthum Dunal (eastern black
nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or
Xanthium strumarium L. (common cocklebur, XANST).
[0064] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in range and pasture. In
certain embodiments, the undesirable vegetation is Amaranthus
palmeri S. Wats. (Palmer amaranth, AMAPA), Ambrosia artemisiifolia
L. (common ragweed, AMBEL), Ambrosia trifida L. (giant ragweed,
AMBTR), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa
auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.)
Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field
bindweed, CONAR), Echinochloa crus-galli (L.) P. Beauv.
(barnyardgrass, ECHCG), Erigeron canadensis L. or Conyza canadensis
(L.) Cronq. (horseweed, ERICA), Euphorbia esula L. (leafy spurge,
EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE),
Plantago lanceolata L. (buckhorn plantain, PLALA), Rumex
obtusifolius L. (broadleaf dock, RUMOB), Salsola tragus L. (Russian
thistle, SASKR), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp
sesbania, SEBEX), Sida spinosa L. (prickly sida, SIDSP), Sinapis
arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial
sowthistle, SONAR), Solanum nigrum L. (black nightshade, SOLNI),
Solanum species (nightshade, SOLSS), Solidago species (goldenrod,
SOOSS), Taraxacum officinale G. H. Weber ex Wiggers (dandelion,
TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica
L. (common nettle, URTDI).
[0065] In some embodiments, the compostions and methods provided
herein are utilized to control undesirable vegetation found in
annual crops and vegetable crops. In certain embodiments, the
undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass,
ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria platyphylla
(Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria
sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa
crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa
colonum (L.) Link (junglerice, ECHCO), Lolium multiflorum Lam.
(Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (Fall
panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI),
Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.)
Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers.
(Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp.
Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow
nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO),
Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species
(pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common
ragweed, AMBEL), Ambrosia psilostachya DC. (Western ragweed,
AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Asclepias
syriaca L. (common milkweed, ASCSY), Chenopodium album L. (common
lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle,
CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE),
Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild
carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL),
Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy
fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.)
Cronq. (Canadian fleabane, ERICA), Helianthus annuus L. (common
sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb.
(smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq.
(ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white
morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce,
LACSE), Portulaca oleracea L. (common purslane, POROL), Sida
spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild
mustard, SINAR), Solanum ptychanthum Dunal (eastern black
nightshade, SOLPT), or Xanthium strumarium L. (common cocklebur,
XANST).
[0066] In some embodiments, the compositions and methods provided
herein are utilized to control undesirable vegetation consisting of
grass, broadleaf and sedge weeds.
[0067] In some embodiments, the compositions and methods are used
to control Agropyron repens L. (quackgrass, AGRRE), Alopecurus
myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.)
Beauv. (windgrass, APESV), Avena sp. (oats, AVESS), Avena
macrocarpa Moench (wild red oat, AVEST), Centaurea cyanus
(cornflower, CENCY), Consolida regalis S. F. Gray (branching
larkspur, CNSRE), Echinochloa crus-galli (L.) P. Beauv.
(barnyardgrass, ECHCG), Galium aparine L. (catchweed bedstraw,
GALAP), Lamium purpureum L. (purple deadnettle, LAMPU), Lolium
multiflorum Lam. (Italian ryegrass, LOLMU), Lolium rigidum (rigid
ryegrass, LOLRI), Lolium L. sp. (ryegrass, LOLSS), Matricaria
recutita L. (wild chamomile, MATCH), Matricaria inodora (scentless
mayweed, MATIN), Papaver rhoeas L. (common poppy, PAPRH), Solanum
nigrum L. (black nightshade, SOLNI), and Stellaria media (L.) Vill.
(common chickweed, STEME), and Viola arvensis Murr. (field violet,
VIOAR).
[0068] In some embodiments, the methods provided herein may be used
to control herbicide resistant or tolerant weeds. The methods
employing the combination of a compound of formula (I) or
agriculturally acceptable ester or salt thereof, florasulam or
agriculturally acceptable salt thereof, and pyroxsulam or
agriculturally acceptable salt thereof, and the compositions
described herein may also be employed to control herbicide
resistant or tolerant weeds. Exemplary resistant or tolerant weeds
include, but are not limited to, biotypes resistant or tolerant to
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitors (e.g., imidazolinones, sulfonylureas,
pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidine
sulfonamides, sulfonylaminocarbonyltriazolinones), photosystem II
inhibitors (e.g., phenylcarbamates, pyridazinones, triazines,
triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles,
phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors
(e.g., aryloxyphenoxy-propionates, cyclohexanediones,
phenylpyrazolines), synthetic auxins (e.g., benzoic acids,
phenoxycarboxylic acids, pyridine carboxylic acids, quinoline
carboxylic acids), auxin transport inhibitors (e.g., phthalamates,
semicarbazones), photosystem I inhibitors (e.g., bipyridyliums),
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors
(e.g., glyphosate), glutamine synthetase inhibitors (e.g.,
glufosinate, bialafos), microtubule assembly inhibitors (e.g.,
benzamides, benzoic acids, dinitroanilines, phosphoramidates,
pyridines), mitosis inhibitors (e.g., carbamates), very long chain
fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides,
oxyacetamides, tetrazolinones), fatty acid and lipid synthesis
inhibitors (e.g., phosphorodithioates, thiocarbamates,
benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase
(PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides,
oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidinediones,
thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors
(e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS)
inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides,
pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase
(HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles,
triketones), cellulose biosynthesis inhibitors (e.g., nitriles,
benzamides, quinclorac, triazolocarboxamides), herbicides with
multiple modes of action such as quinclorac, and unclassified
herbicides such as arylaminopropionic acids, difenzoquat,
endothall, and organoarsenicals. Exemplary resistant or tolerant
weeds include, but are not limited to, biotypes with resistance or
tolerance to single or multiple herbicides, biotypes with
resistance or tolerance to single or multiple chemical classes,
biotypes with resistance or tolerance to single or multiple
herbicide modes of action, and biotypes with single or multiple
resistance or tolerance mechanisms (e.g., target site resistance or
metabolic resistance).
[0069] The compositions and methods described herein are used to
control undesirable vegetation in glyphosate-, 2,4-D- and
glufosinate-tolerant cereals, corn, or sorghum which may also be
combined with traits providing dicamba-tolerance (e.g., DMO),
pyridyloxy auxin-tolerance (e.g., aad-12, aad-13), auxin-tolerance,
auxin transport inhibitor-tolerance, acetyl CoA carboxylase
(ACCase) inhibitor-herbicide tolerance [e.g.,
aryloxyphenoxypropionate, cyclohexanedione, and phenylpyrazoline
chemistries (e.g., various ACCase genes and aad-1 gene)],
acetolactate synthase (ALS)-inhibiting herbicide tolerance (e.g.,
imidazolinone, sulfonylurea, triazolopyrimidine sulfonamide,
pyrmidinylthiobenzoate, and other chemistries=AHAS, Csrl, SurA),
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerance,
phytoene desaturase (PDS) inhibitor-tolerance (e.g., pds, CYP1A1,
CYP2B6, CYP2C19), carotenoid biosynthesis inhibitor-tolerance,
protoporphyrinogen oxidase (PPO) inhibitor-tolerance, cellulose
biosynthesis inhibitor-tolerance (e.g., ixr2-1, CYP1A1), mitosis
inhibitor-tolerance, microtubule inhibitor-tolerance, very long
chain fatty acid (VLCFA) inhibitor-tolerance (e.g., CYP1A1, CYP2B6,
CYP2C19), fatty acid and lipid biosynthesis inhibitor-tolerance
(e.g., CYP1A1), photosystem I inhibitor-tolerance (e.g., SOD),
photosystem II inhibitor (triazine, nitrile, and phenylurea
chemistries) tolerance (e.g., psbA, CYP1A1, CYP2B6, CYP2C19, and
Bxn), in crops (such as, but not limited to, corn, canola/oilseed
rape, rice, cereals, sorghum, sunflower, sugar beet, sugarcane, and
turf), for example, in conjunction with glyphosate,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy
auxins, synthetic auxins, auxin transport inhibitors,
aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines,
ACCase inhibitors, imidazolinones, sulfonylureas,
pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidine
sulfonamides, sulfonylaminocarbonyltriazolinones, ALS or
acetohydroxy acid synthase (AHAS) inhibitors, HPPD inhibitors, PDS
inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors,
cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule
inhibitors, very long chain fatty acid inhibitors, fatty acid and
lipid biosynthesis inhibitors, photosystem I inhibitors,
photosystem II inhibitors, triazines, and bromoxynil. The
compositions and methods may be used in controlling undesirable
vegetation in cereals, soybeans, corn, or cotton possessing single
and multiple or stacked traits conferring tolerance to single or
multiple chemistries and/or inhibitors of multiple modes of
action.
[0070] The described embodiments and following examples are for
illustrative purposes and are not intended to limit the scope of
the claims. Other modifications, uses, or combinations with respect
to the compositions described herein will be apparent to a person
of ordinary skill in the art without departing from the spirit and
scope of the claimed subject matter.
EXAMPLES
Example 1. Evaluation of Herbicidal Activity of Mixtures Under
Field Conditions
[0071] Methodology
[0072] Eleven small plot field trials were established across
various ecozones in Belgium, Germany, Hungary, Morocco, Poland,
Spain, Tunisia and Turkey, between 2010 and 2014 to evaluate
potential synergy between 1) florasulam (250 WG and 50 grams active
ingredient per liter (g ai/L)) plus 2) halauxifen-methyl (200 WG,
100 WG, 95.9 grams acid equivalent per liter (g ae/L) SC and 7.5 g
ae/L EC) plus 3) pyroxsulam (75 WG) when applied in three-way
combinations. Two-way combinations were applied as
florasulam+halauxifen-methyl (200 WG and 8.75 gr ae/L OD) in
combination with pyroxsulam (75 WG as "PERUN" and 450D as
"PALLUS"). Except for the trials utilizing the OD formulations,
Actirob B was applied at 0.5 or 1.0 liters per hectare (L/ha), or
Polyglycol 26-2 was applied at 0.5 to 1.0 L/ha in all respective
single and tankmixture treatments being evaluated.
[0073] Trials were established as randomized complete blocks (RCBD)
with three to four replicates. Individual treatments were 2-2.5
meters (m) wide and 6-20 m long. An untreated control was included
in each trial. All trial sites had naturally occurring populations
of weeds. Wheat trials (Triticum aestivum) were generally planted,
depending on the country and normal time of planting, from
September to November, and herbicide treatments were applied during
the normal spring timing from January to April.
[0074] Herbicides were applied with backpack or bicycle sprayers
using compressed air, nitrogen (N.sub.2) or carbon dioxide
(CO.sub.2) as a propellant. All sprayers delivered a uniform spray
pattern that provided thorough coverage of the foliage using a
water volume of 150-300 L/ha. All herbicides were applied
post-emergence in the spring to early-summer At the time of
herbicide applications, winter wheat crops were at the six-leaf to
three-tiller stage. Broadleaf and grass weeds were at a similar
stage of growth at the time of herbicide application, typically
from five leaf to 3 tiller depending on the weed species and time
of year.
[0075] Evaluation
[0076] The treated plots and control plots were rated blind at
various intervals after application. Ratings were based on a
Percent (%) Visual basis, where 0 corresponds to no visual effect
as seen as exemplified by weed control or crop injury and 100
corresponds to complete kill of the target weeds or complete crop
injury. The control of the target weeds was visually assessed as
percent control, compared to an untreated control plot. The
assessments were based on a percent visual reduction in pest plant
biomass and/or stand reduction of weed population. In general,
three-to-four replicates were assessed for each treatment, and the
results for each experiment (trial) are presented as overall
average control.
[0077] The efficacy of all treatments was assessed at 13-22 days
after application (DAA) for an early season rating, 23-39 DAA for a
mid-season rating, and 41-84 DAA for a late-season rating. The data
were statistically analyzed using various statistical methods,
generally including a Tukey's HSD Factorial Analysis of Variance
with a significance level of 5%.
[0078] Data were collected for all trials and analyzed using
various statistical methods.
[0079] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. Calculation of the
synergistic and antagonistic response of herbicide combinations.
Weeds 1967, 15, 20-22). A t-test (alpha=0.05) between Colby
predictions and observed combinations was used to test for
significant differences indicating synergy or antagonism using
replicate data. The results presented in the Tables were
significant according to the described criteria.
[0080] The following equation was used to calculate the expected
activity of mixtures containing three active ingredients, A. B, and
C:
Expected=A+B+C-(AB+AC+BC)/100+(ABC)/10,000
[0081] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture;
[0082] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture;
[0083] C=observed efficacy of active ingredient C at the same
concentration as used in the mixture.
[0084] Some experiments described herein were performed such that
active ingredients A and B were combined and only the efficacy of
the combination was determined. As such, Colby's equation
simplifies to
Expected=Z+C-(ZC/100)
[0085] Z=observed efficacy of a combination of active ingredient A
(the compound of formula (I) or agriculturally acceptable ester or
salt thereof) and active ingredient B (florasulam or agriculturally
acceptable salt thereof) at the same concentration as used in the
mixture;
[0086] C=observed efficacy of active ingredient C (pyroxsulam or
agriculturally acceptable salt thereof) at the same concentration
as used in the mixture.
[0087] The results are summarized in Tables 1-4.
TABLE-US-00001 TABLE 1 Herbicidal Broadleaf Weed Control (% Visual
Control) from Three-Way Tank Mixtures of Halauxifen-Methyl +
Florasulam + Pyroxsulam in Multiple Field Trials at 14 to 56 Days
After Application (DAA). Combination Halauxifen- Colby Methyl
Florasulam Pyroxsulam Observed Predicted Weed Mean % Mean % Mean %
Mean % Mean % Bayer Evaluation Weed Weed Weed Weed Weed Code
Interval g ae/ha Control g ai/ha Control g ai/ha Control Control
Control MATIN 14DAA 3 0.0 4 35.0 12 20.0 50.0 48.0 MATIN 14DAA 4
0.0 3 30.0 12 20.0 65.0 44.0 VIOAR 14DAA 3 0.0 3 0.0 12 61.3 83.8
61.3 VIOAR 14DAA 4 0.0 3 0.0 12 61.3 78.8 61.3 LAMPU 15DAA 4.8 72.5
3.75 0.0 12 10.0 95.0 75.3 LAMPU 15DAA 6 55.0 3.75 0.0 12 10.0 95.0
59.6 LAMPU 15DAA 4.8 72.5 3.75 0.0 9.6 16.3 95.0 76.9 LAMPU 15DAA 6
55.0 3.75 0.0 9.6 16.3 95.0 62.3 MATCH 15DAA 4.8 0.0 3.75 10.0 9.6
12.8 32.5 21.5 STEME 15DAA 4.8 0.0 3.75 0.0 12 0.0 23.8 0.0 STEME
15DAA 6 0.0 3.75 0.0 12 0.0 26.3 0.0 STEME 15DAA 4.8 0.0 3.75 0.0
9.6 0.0 32.5 0.0 STEME 15DAA 6 0.0 3.75 0.0 9.6 0.0 23.8 0.0 CENCY
28DAA 3 75.0 3 48.8 12 38.8 99.5 92.2 CENCY 28DAA 3 75.0 4 75.0 12
38.8 99.8 96.1 GALAP 28DAA 3 0.0 3 57.5 12 89.5 99.5 95.6 SOLNI
29DAA 3 10.0 6.25 40.0 18.75 50.0 90.0 73.0 CNSRE 31DAA 3 68.3 4
75.0 12 66.8 99.5 97.4 CNSRE 31DAA 4 70.8 3 75.0 12 66.8 100.0 97.6
CNSRE 31DAA 4 70.8 4 75.0 12 66.8 100.0 97.6 CNSRE 53DAA 3 70.0 3
78.5 12 70.0 100.0 98.1 CNSRE 53DAA 3 70.0 4 79.5 12 70.0 100.0
98.2 CNSRE 53DAA 4 72.0 3 78.5 12 70.0 100.0 98.2 CNSRE 53DAA 4
72.0 4 79.5 12 70.0 100.0 98.3 CENCY 56DAA 3 2.5 3 27.5 12 15.0
57.5 39.8 CENCY 56DAA 3 2.5 4 30.0 12 15.0 62.5 42.4 CENCY 56DAA 3
83.8 3 48.8 12 32.5 99.5 94.1 CENCY 56DAA 3 83.8 4 83.8 12 32.5
99.8 98.1 SOLNI 56DAA 3 0.0 6.25 20.0 18.75 30.0 90.0 44.0 VIOAR
56DAA 3 0.0 4 20.0 12 93.8 99.5 95.1
TABLE-US-00002 TABLE 2 Herbicidal Broadleaf Weed Control (% Visual
Control) from Three-Way Tank Mixtures of Halauxifen-Methyl +
Florasulam + Pyroxsulam in Multiple Field Trials at 61 to 84 Days
After Application (DAA). Combination Halauxifen- Colby Methyl
Florasulam Pyroxsulam Observed Predicted Weed Mean % Mean % Mean %
Mean % Mean % Bayer Evaluation Weed Weed Weed Weed Weed Code
Interval g ae/ha Control g ai/ha Control g ai/ha Control Control
Control MATCH 61DAA 4.8 0.0 3.75 85.0 12 20.0 98.0 88.1 MATCH 61DAA
6 1.3 3.75 85.0 12 20.0 98.3 88.2 MATCH 61DAA 4.8 0.0 3.75 85.0 9.6
16.3 98.3 87.5 MATCH 61DAA 6 1.3 3.75 85.0 9.6 16.3 98.0 87.6 MATCH
61DAA 4.8 0.0 3.75 67.4 12 26.3 81.9 76.0 MATCH 61DAA 6 3.2 3.75
67.4 12 26.3 82.5 76.7 MATCH 61DAA 4.8 0.0 3.75 67.4 9.6 23.7 82.5
75.1 MATCH 61DAA 6 3.2 3.75 67.4 9.6 23.7 81.9 75.9 STEME 61DAA 4.8
0.0 3.75 68.8 12 3.8 98.8 69.9 STEME 61DAA 6 1.3 3.75 68.8 12 3.8
98.3 70.2 STEME 61DAA 4.8 0.0 3.75 68.8 9.6 5.0 99.8 70.4 STEME
61DAA 6 1.3 3.75 68.8 9.6 5.0 98.3 70.7 STEME 61DAA 4.8 0.0 3.75
56.1 12 9.7 84.5 60.4 STEME 61DAA 6 3.2 3.75 56.1 12 9.7 84.7 61.5
STEME 61DAA 4.8 0.0 3.75 56.1 9.6 11.1 88.6 61.0 STEME 61DAA 6 3.2
3.75 56.1 9.6 11.1 83.9 62.2 CENCY 77DAA 3 82.5 3 40.0 12 15.0 99.5
91.3 CENCY 77DAA 3 82.5 4 82.5 12 15.0 99.8 97.5 MATCH 78DAA 4.8
6.3 3.75 76.3 12 18.8 98.8 81.5 MATCH 78DAA 6 6.3 3.75 76.3 12 18.8
98.8 81.5 MATCH 78DAA 4.8 6.3 3.75 76.3 9.6 17.0 98.8 81.4 MATCH
78DAA 6 6.3 3.75 76.3 9.6 17.0 98.8 81.4 STEME 78DAA 4.8 6.3 3.75
31.3 12 13.8 98.8 44.6 STEME 78DAA 6 8.8 3.75 31.3 12 13.8 98.5
46.2 STEME 78DAA 4.8 6.3 3.75 31.3 9.6 16.3 99.0 46.2 STEME 78DAA 6
8.8 3.75 31.3 9.6 16.3 98.3 47.8 CENCY 84DAA 3 1.3 4 30.0 12 12.5
62.5 39.2 CENCY 84DAA 4 27.5 4 30.0 12 12.5 71.3 55.5 CNSRE 84DAA 3
70.0 3 79.0 12 70.0 100.0 98.1 CNSRE 84DAA 3 70.0 4 80.0 12 70.0
100.0 98.2 CNSRE 84DAA 4 72.5 3 79 12 70 100 98.3 CNSRE 84DAA 4
72.5 4 80 12 70 100 98.4
TABLE-US-00003 TABLE 3 Herbicidal Grass Weed Control (% Visual
Control) from Three-Way Tank Mixtures of Halauxifen-Methyl +
Florasulam + Pyroxsulam in Multiple Field Trials at 14 to 56 Days
After Application (DAA). Combination Halauxifen- Colby Methyl
Florasulam Pyroxsulam Observed Predicted Weed Mean % Mean % Mean %
Mean % Mean % Bayer Evaluation Weed Weed Weed Weed Weed Code
Interval g ae/ha Control g ai/ha Control g ai/ha Control Control
Control AGRRE 14DAA 3 0.0 4 0.0 12 37.5 78.8 37.5 ALOMY 15DAA 4 0.0
3 2.5 12 27.5 55.0 28.8 APESV 14DAA 3 0.0 3 0.0 12 72.5 91.3 72.5
APESV 14DAA 3 0.0 4 0.0 12 72.5 90.8 72.5 APESV 14DAA 4 0.0 3 0.0
12 72.5 90.8 72.5 APESV 14DAA 4 0.0 4 0.0 12 72.5 92.0 72.5 APESV
28DAA 3 0.0 3 0.0 12 88.8 99.5 88.8 APESV 28DAA 3 0.0 4 0.0 12 88.8
96.3 88.8 APESV 28DAA 4 0.0 3 0.0 12 88.8 96.3 88.8 APESV 28DAA 4
0.0 4 0.0 12 88.8 98.8 88.8 APESV 56DAA 3 0.0 3 0.0 12 94.5 100.0
94.5 APESV 56DAA 3 0.0 4 0.0 12 94.5 98.8 94.5 ECHCG 14DAA 3 0.0
6.25 20.0 18.75 85.0 90.0 88.0 ECHCG 29DAA 3 0.0 6.25 10.0 18.75
75.0 80.0 77.5 ECHCG 56DAA 3 0.0 6.25 10.0 18.75 60.0 75.0 64.0
TABLE-US-00004 TABLE 4 Herbicidal Grass and Broadleaf Weed Control
(% Visual Control) from Two-Way Tank Mixtures of Halauxifen- Methyl
+ Florasulam and Pyroxsulam in Multiple Field Trials at 14 to 78
Days After Application (DAA). Combination Halauxifen- Colby Methyl
+ Pyroxsulam Meas- Pre- Florasulam Mean ured dicted Weed Eval- Mean
% % Mean % Mean % Bayer uation Weed g Weed Weed Weed Code Interval
g ai/ha Control ai/ha Control Control Control LOLSS 14DAA 10 0.0
18.75 90.0 92.8 90.0 LAMPU 15DAA 9.75 72.5 12 10.0 95.0 75.3 LAMPU
15DAA 9.75 72.5 9.6 16.3 95.0 76.9 STEME 15DAA 8.55 23.8 9.6 0.0
32.5 23.8 LOLMU 28DAA 10.5 0.0 22.5 72.5 82.5 72.5 LOLRI 28DAA 8
0.0 22.5 72.5 92.5 72.5 SOLNI 29DAA 9.25 40.0 18.75 50.0 90.0 70.0
AVEST 32DAA 10 0.0 18.75 97.8 100.0 97.8 LAMPU 32DAA 9.75 95.3 9.6
0.0 96.3 95.3 LOLMU 55DAA 10.5 0.0 22.5 72.5 85.0 72.5 LOLMU 55DAA
8.75 0.0 22.5 72.5 85.0 72.5 PAPRH 56DAA 8.75 98.8 22.5 1.9 100.0
98.8 SOLNI 56DAA 9.25 30.0 18.75 30.0 90.0 51.0 AVESS 76DAA 11 2.5
18.75 62.0 91.5 63.1 STEME 78DAA 8.55 98.0 9.6 16.3 99.0 98.3
[0088] The following abbreviations are used in the tables
above:
halauxifen-methyl=methyl ester of
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxyl-
ic acid or methyl
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxyl-
ate
florasulam=N-(2,6-difluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo
[1,5-c]pyrimidine-2-sulfonamide
[0089]
pyroxsulam=N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2--
methoxy-4-(trifluoromethyl)-pyridine-3-sulfonamide
AGRRE=Agropyron repens L. (quackgrass) ALOMY=Alopecurus myosuroides
Huds. (blackgrass) APESV=Apera spica-venti (L.) Beauv. (windgrass)
AVESS=Avena sp. (oats) AVEST=Avena macrocarpa Moench (wild red oat)
CENCY=Centaurea cyanus (cornflower) CNSRE=Consolida regalis S. F.
Gray (branching larkspur) ECHCG=Echinochloa crus-galli (L.) P.
Beauv. (barnyardgrass) GALAP=Galium aparine L. (catchweed bedstraw)
LAMPU=Lamium purpureum L. (purple deadnettle) LOLMU=Lolium
multiflorum Lam. (Italian ryegrass) LOLRI=Lolium rigidum (rigid
ryegrass) LOLSS=Lolium L. sp. (ryegrass) MATCH=Matricaria recutita
L. (wild chamomile) MATIN=Matricaria inodora (scentless mayweed)
PAPRH=Papaver rhoeas L. (common poppy) SOLNI=Solanum nigrum L.
(black nightshade) STEME=Stellaria media (L.) Vill. (common
chickweed) VIOAR=Viola arvensis Murr. (field violet) g ae/ha=grams
acid equivalent per hectare g ai/ha=grams active ingredient per
hectare
DAA=Days After Application
[0090] The compositions and methods of the appended claims are not
limited in scope by the specific compositions and methods described
herein, which are intended as illustrations of a few aspects of the
claims and any compositions and methods that are functionally
equivalent are intended to fall within the scope of the claims.
Various modifications of the compositions and methods in addition
to those shown and described herein are intended to fall within the
scope of the appended claims. Further, while only certain
representative composition materials and method steps disclosed
herein are specifically described, other combinations of the
composition materials and method steps also are intended to fall
within the scope of the appended claims, even if not specifically
recited. Thus, a combination of steps, elements, components, or
constituents may be explicitly mentioned herein; however, other
combinations of steps, elements, components, and constituents are
included, even though not explicitly stated. The term "comprising"
and variations thereof as used herein is used synonymously with the
term "including" and variations thereof and are open, non-limiting
terms. Although the terms "comprising" and "including" have been
used herein to describe various embodiments, the terms "consisting
essentially of" and "consisting of" can be used in place of
"comprising" and "including" to provide for more specific
embodiments of the invention and are also disclosed.
* * * * *